Abstract
Various derivatives of 2-phenylpyrrole were condensed with squaric acid to give the corresponding squaraines. The products are drawn with the anti geometry rather than the syn geometry generally shown in the past: the arguments for this formulation are given, including the analogy with 2,5-bis(4-ethyl-3,5-dimethylpyrrol-2-yl)-1,4-benzoquinone, for which an X-ray structure is presented. Solutions of the new bis(5-arylpyrrol-2-yl)squaraines have intense, sharp absorption bands shifted to the red. Condensation of squaric acid with arylpyrroles possessing fused ring systems, and condensation with 2-styrylpyrrole, gave chromophores with high values for λ max and ɛ max. Certain of these chromophores appear to be suitable for further structural elaboration to give materials having potential in optoelectronic and photodynamic applications.
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